Revitalized Chestertown Marina One of the Headliners for Downrigging Weekend 2018


The Sultana Education Foundation has announced the schedule for its annual Downrigging Weekend Tall Ship and Wooden Boat Festival, set for October 26–29, in Chestertown, Maryland.  Now in its 18th year, Downrigging Weekend is one of the largest annual tall ship gatherings in North America and features four days of tall ship sails, deck tours, concerts, lectures, films exhibits and family activities.


Unique among tall ship festivals on the East Coast, Downrigging Weekend offers visitors the opportunity sail on a fleet of tall ships. Over the course of Downrigging Weekend, an impressive array of historic vessels—including KALMAR NYCKEL (the state ship of Delaware), the schooners VIRGINIA, LYNX, LADY MARYLAND, and SULTANA, and skipjacks SIGSBEE and ELSWORTH—will take passengers out for four joint sails on the Chester River. Sailing tickets begin at $25 and are available at Visitors can also visit and tour the ships at the dock during one of several scheduled free open houses.  Those looking for more comfort for their voyage on the Chester also have the opportunity to cruise on Chestertown’s own River Packet.

This year’s event will serve also as the unveiling for Chestertown’s newly revitalized waterfront. Following two years of construction, and $6.2 million in improvements, visitors to Downrigging will be welcomed by larger, state-of-the-art floating piers, a raised parking lot, a new Marina office, public bathrooms and showers, and extensive landscaping.

The Downrigging Weekend festivities won’t stop at the water’s edge.  This year’s events will feature the return of the Delmarva Dock Dogs competition hosted by Kingstown Farm, Home and Garden. Taking place on both Saturday and Sunday, this competition will see dogs from all over the region compete to see who can leap the furthest. Local dog owners are welcome to enter their dogs in the competition and registration and scheduling information can be found at

The Festivals’ on-the-water events will be rounded out by an exhibit of Classic Cars and Boats on the waterfront in conjunction with the Antique & Classic Boat Society, a waterside 5K and half-marathon hosted by the Chester River Association, and concerts by The Eastport Oyster Boys, Levi Stephens, and the High and Wides. Visitors this year won’t have to leave the River to hear music, thanks to a new waterfront stage hosting performances by Betty and the Bullet, the Mountain Lion String Band, the Chestertown Ukulele Club, Apache Trails, and the Dovetail Trio.

For those interested in maritime history, lectures will take place throughout the weekend.  On Friday evening, John Brady, President and CEO of the Independence Seaport Museum, will talk about the 1892 cruiser OLYMPIA. Saturday afternoon, Press Harding will perform “Boy in the Boatyard,” a performance of music, spoken word and images inspired by his childhood in Wingate, Maryland, and the Bookplate will host a talk on Gilbert Byron and his work by author Jacques T. Baker.

Art will be a major theme for Downrigging, including an exhibit by Marc Castelli, “Minding the Dogvane,” at the Carla Massoni Gallery, as well as the Artworks annual Studio Tour. The Kent County Arts Council has produced a new play specifically for Downrigging Weekend by playwright Earl Price, “Unlading,” which tells the story 23 enslaved Africans as they are “unladed” from a Dutch Man of War.

Also back this year is the enormously popular annual nighttime illumination of the tall ships and fireworks display over Chestertown’s historic harbor.

For a full schedule, or to register for a Downrigging Weekend sail, please visit


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